For Ineffective Assistance in Plea, Sentencing: Think Prejudice

By Aditi Mukherji, JD on January 16, 2014 | Last updated on March 21, 2019

Convicted mail fraudster Larry Covington alleged that his trial counsel was ineffective at two stages of his proceedings. Covington alleges that § 2C1.1 of the United States Sentencing Guidelines did not apply to his conduct and that his counsel should have challenged its application to his convictions both during plea negotiation and at sentencing.

Ultimately, the three-member panel of the Eighth Circuit determined that Covington's arguments floundered when it came to proving prejudice. They didn't even reach the question of whether his attorney was in fact deficient. The case highlights how the Eighth Circuit handles claims of ineffective assistance of counsel in the context of plea negotiations and sentencing.

Plea Negotiation

Even assuming that Covington's lawyer was deficient during plea negotiations by agreeing to application of the wrong set of guidelines -- § 2C1.1 instead of § 2B1.1 -- Covington failed to show this deficiency prejudiced him, according to the panel.

In order to satisfy the "prejudice" requirement for ineffective assistance of counsel, the defendant must show that there is a reasonable probability that, but for counsel's errors, he would not have pleaded guilty and would have insisted on going to trial.

In this case, Covington failed to demonstrate prejudice in his plea negotiation in three ways:

  • He failed to demonstrate, or even allege, that had his attorney informed him that § 2C1.1 was not the proper Guidelines section, he would not have pleaded guilty and would have demanded a trial;
  • He never showed that going to trial would have resulted in a lower sentence; and
  • He failed to address the fact that his plea negotiations actually got him a pretty good deal. In exchange for Covington's guilty plea, the government agreed to dismiss the remaining forty-seven counts of the indictment.


Covington further contended that his counsel was ineffective at sentencing because his attorney should have objected to the application of § 2C1.1. But the prejudice problem haunted him yet again, proving the demise of his sentencing argument.

The problem here was that the plea agreement stated the parties could advocate their positions at the hearing on issues not yet agreed upon -- but alas, the application of § 2C1.1 was agreed upon.

The panel pointed out that if Covington's attorney had objected to an agreed upon guidelines section, his attorney would have breached the plea agreement, a binding contract. Then all bets would be off with the plea deal and the Feds would be able to pursue the forty-seven counts they had agreed to dismiss.

At bottom, Covington's counsel could not argue the issue at sentencing without breaching the plea agreement and exposing Covington to possible prejudice; as a result, Covington could not demonstrate that he was prejudiced by his counsel's failure to object to application of the section at sentencing.

Prejudice: it will make or break an ineffective assistance of counsel argument.

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